Calixarene and hemicarcerand-like compounds obtained by self-assembly of 3-aminophenylboronic acid and salicylaldehyde derivatives

• One-pot synthesis of calixarene and hemicarcerand-like compounds.
• High cone conformation selectivity.
• Modulation of hydrophobic or hydrophilic properties by changing the aromatic substituents.
• Modulation of the size cavity for hemicarcerands by changing the size of the linkers.

One-pot synthesis of calixarene and hemicarcerand like compounds can be modulated by use of mono- or bis-salicylaldehyde derivatives respectively, reacting with 3-aminophenylboronic acid. Thus, the first part of this work is focused on the synthesis of calix-like compounds derived from salicylaldehyde units including different substituents on the aromatic moiety. Seven different calix structures are described and their structural analysis has been carried out by spectroscopic techniques. The second part corresponds to the description of bis-salicylaldehyde derivatives, synthesis and reactivity towards the 3-aminophenylboronic acid leading to the formation of hemicarcerand-like compounds. Aliphatic and aromatic chains were inserted as linkers between the two salicylaldehyde units in order to evaluate the influence on the formation of the hemicarcerands compounds. Both, calixarene and hemicarcerand compounds resulted from condensation reactions, wherein the formation of N–B coordination bonds plays a significant role on the macrocyclization process.

One-pot synthesis of calixarene and hemicarcerand like compounds can be modulated by use of mono- or bis-salicylaldehyde derivatives, respectively reacting with 3-aminophenylboronic acid. Both, calixarene and hemicarcerand compounds are result from condensation reactions, wherein the formation of N–B coordination bonds plays a significant role on the formation of macrocyclic products.Figure optionsDownload as PowerPoint slide